Transformation of compounds containing C-N bonds on heterogeneous catalysts. Part V.1 1 Part IV. J. Mol. Catal., 49 (1988) 103. Hydrogenolysis of C-N bonds in substituted azacycloalkanones: preparation of sterically hindered amines and amino derivatives

György Göndös, Lajos Gera, Mihály Bartók

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Abstract

On various transition metal catalysts (Raney nickel, Pd/C, Pd black, RuO2, Rh/C), the N-C(2) bond in N-benzoyl-2,2,4,4-tetraMe-azetidin-3-one (1) undergoes hydrogenolysis with 100% selectivity, as does that in the corresponding azetidine derivative 2 on Raney nickel; in the process, the oxo group in the ring in 1 is converted to a hydroxy group. In the analogues with higher numbers of ring atoms, only the latter hydrogenation proceeds; under identical reaction conditions, C-N hydrogenolysis does not occur. The rate of hydrogenolysis is increased by the carbonyl group at position 3 in azetidinone, as compared to that of azetidine, which does not possess the carbonyl function. A proposal is made concerning the reaction mechanism.

Original languageEnglish
Pages (from-to)81-89
Number of pages9
JournalJournal of molecular catalysis
Volume57
Issue number1
DOIs
Publication statusPublished - 1989

ASJC Scopus subject areas

  • Engineering(all)

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